Our research on intramolecular effects on electron transfer reactions is devoted to a study of how neighboring nucleophiles influence the redox chemistry of organosulfur compounds. The reason that organosulfur compounds were chosen is that sulfur is highly polarized, it readily assumes a positive charge and it can increase its coordination number to greater than four. Specifically we are examining how neighboring groups affect the rate, the kinetics and the product distribution and stereoselectivity associated with thioether sulfoxide interconversions. We have examined the I2 oxidation and HI reduction of systems containing neighboring thioether, amine and alcohol groups and we are beginning a study of the aqueous I2 oxidation of l-oxa-5-thiacyclooctane to see the effect of a neighboring ether group. We have prepared 3,5-dimethyl-4-hydroxybenzylmethyl sulfide to evaluate the ability of an activated aromatic compound to interact with sulfur. In addition to I2 oxidations, we plan to use NOBF 4 as an oxidizing agent, where appropriate to determine if cation radicals or dications are formed. Various phenol derivatives where the thioether group is separated further from the aromatic ring are also being prepared. Thioethers and sulfoxides containing neighboring imidazole and other ring systems containing multiple heteroatoms are also under investigation.